Toluene → HCID 20361795, compound

HRID 1580304Notes

Reaction equation

HRID 1580304 reaction equation
[NH2-].[Na+].C1(C)C=CC=CC=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]#[N:19])=[CH:13][CH:12]=1.Cl[C:21]1[S:22][CH:23]=[CH:24][N:25]=1>O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([C:21]2[S:22][CH:23]=[CH:24][N:25]=2)[C:18]#[N:19])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 24533Sodium amideHCID 764292-ChlorothiazoleHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 20361795HCID 20361795, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

At 0°-5°C add a suspension of 28.5 g. of sodamide in 300 ml. of toluene to a stirred solution containing 50 g. of p-chlorphenylacetonitrile and 40 g. of 2-chlorothiazole in 400 ml. of toluene. Maintain the temperature at 20°C for 2 hrs. and finally at 60°C. for 1 hr. Consecutively add 100 ml. of water and 35 ml. of acetic acid at 0°-10°C and filter the resulting mixture. Separate the toluene layer, concentrate in vacuo and distill the residue to give α-(p-chlorphenyl)-2-thiazolylacetonitrile as a mobile yellow oil, b.p. 155°-160°C/1 mm.

Workup

  1. additionAt 0°-5°C add
  2. additiona suspension of 28.5 g
  3. filtrationof acetic acid at 0°-10°C and filter the resulting mixture
  4. customSeparate the toluene layer
  5. concentrationconcentrate in vacuo
  6. distillationdistill the residue

Sources & evidence

ORD record
ord-adca18d7702b4f8691a0c6c04fac8dad
Source dataset
uspto-grants-1976_01
Patent number
US03932431

Reaction notes

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